1,2,4-Triazole-3-thione reacts with 1-adamantanol in concentrated sulfuric acid to form 1-(1-adamantyl)-1,2,4-triazole-3-thione, which transforms into 1-(1-adamantyl)-3-(1-adamantyl)sulfanyl-1,2,4-triazole or is oxidized with atmospheric oxygen dissolved in sulfuric acid into 3,3′-disulfanediylbis[1-(1-adamantyl)- 1,2,4-triazole]. 3-(1-Adamantyl)sulfanyl-1,2,4-triazole was prepared by adamantylation...
Acid-catalyzed N-adamanthylation of C-C-linked pyrazolyl- and tetrazolylpyrazoles in H3PO4- AcOH (4:1) or H2SO4 involves, depending on conditions, one or both rings. The mutual effect of the rings is weak. C-N-Linked azolylpyrazoles are a conjugated system, and the formation of N-adamanthyl derivatives is strongly affected by the second azolyl ring.
3-R-1,2,4-Triazol-5-ones are adamantylated in sulfuric acid. The reaction involves the N1 atom of the ring. 4-Adamantyl-1-methyl-, 1-adamantyl-4-methyl-, and 1,4-diadamantyl-1,2,4-triazol-5-ones were also prepared. Therewith, it was found that N1 exhibits a higher reactivity than N4.
Adamantylation of indazole and its C-nitro derivatives with 1-hydroxyadamantane in mineral acids yields exclusively the corresponding 1-(1-adamantyl)indazoles via attack by 1-adamantyl cation on the protonated substrate. The oxidative alkylation with 1-iodoadamantane leads to formation of 1- and 2-(1-adamantyl)indazoles, the 2-isomer prevailing.
Pyrazoles with pKBH+ no more than 0.8 and having substituents in 3(5) position with effective van der Waals radii not exceeding 2 Å in a mixture of phosphoric and acetic acids at weight ratio 4:1 (H0 -1,8) react with 1-adamantanol to afford the corresponding 1-(1-adamantyl)- or 1,4-di(1-adamantyl)pyrazoles.
Potassium amidosulfate reacts with formaldehyde at pH 7-12 to afford a mixture of dipotassium 4-hydroxy-1,3-diazabutane-1,3-disulfonate hydrate and tripotassium 6-hydroxy-1,3,5-triazahexane-1,3,5-trisulfonate HO(CH2NSO3K)n·H2O (n = 2, 3). The reaction of the same compounds at pH 1-3 gives diammonium 1,3,5,7-tetraazabicyclo[3.3.1]nonane-3,7-disulfonic acid sulfate dihydrate.
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